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Progress with Tuscany itinerary

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We are making some progress narrowing down where to go for our 2 week Tuscany trip. We love to have great food, wine, walk, see the sights, absorb the ambience, drive around and explore. We want to stay in a combination of city and country accomodations. We like to stay in places where there are great dinner restaurants so that we don't have to drive in unfamiliar places at night. We hope to find good base areas so that we can drive and explore things during the day.

Here is what we've come up with--I welcome any suggestions:
Florence--3 nights
Rent car, drive to San Gimignano for 1 night
Siena 2 nights
Southern Tuscany area 2 nights--stay in Pienza? Montepulciano? somewhere else?
Go to Cortona/Arezzo area stay there or somewhere else?
Go to Assisi/Spoleto area--where to stay?

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